I have successfully cut circles with a router and circle cutting jig. The hole doesn’t have to go clear through, just make it the bottom. I would make the bevel on the router table with a guide pin.
Yep, my plan is to have a small vertical band on the top edge with the chamfer below.Another thing to think about - that acute angle will be very prone to chip out or splinters in use. It will also be tough to hold up any kind of 'film' finish. I would suggest that you either round it over or a small vertical cut-off of the angle, and account for the waste in your dimensions.
Hopefully we will be seeing pictures of the jigs also.Just a quick update on this project - I ended up making a table saw circle jig and a router circle jig. I used the former to cut out the circle, including the chamfer, in one step. I used the latter to route a ring-shaped groove in the bottom of the piece of the bearing to sit in. Nice to have both on hand as I designed them in a way that will let me cut a wide range of circle sizes with the same jigs. Thanks to all for your input.